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How To Style An Oversized Shirt – 32 Outfit Ideas To Copy

How To Style An Oversized Shirt – 32 Outfit Ideas To Copy

How To Style An Oversized Shirt - 20 Outfit Ideas & Styling Tips | Travel Beauty Blog

How To Style An Oversized Shirt + 32 Outfit Ideas For Inspiration

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How to distinguish an oversized shirt or tee from a regular fit?

An oversized shirt is baggy, loose fitting and usually falls below the waist for a relaxed fit.

Ideally, it should be 2-3 sizes bigger.

They are no doubt wardrobe staples as they are very versatile pieces that can be dressed up or down depending on the occasion.

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Although most times this style alludes to the classic white button-down shirt, we have also incorporated some oversized blazers, sweaters, blouses and coats for inspiration.

Read along for some quick and easy styling tips on how to style an oversized shirt.

From casual day time looks, to dressy, elegant styles for an evening or night out.

1. Oversized Shirt and Leather Shorts

How To Style An Oversized Satin Shirt:

For a minimalistic look, pair a white oversized satin shirt loosely tucked inside black leather shorts.

Accessorize with a black statement mini bag and sunglasses for day time wear.

Finish off the look with a pair of black strappy heeled sandals or pumps.

How To Style An Oversized Shirt - 10 Styling Tips | Travel Beauty Blog
Photo: Depositphotos
How To Style An Oversized Shirt - 32 Outfit Ideas To Copy

2. Oversized Fuchsia Pink Shirt with Black Jeans

How To Style An Oversized Shirt (Pink):

Bright pink oversized monogram print shirt fully inserted inside a pair of black jeans.

This ensemble doesn’t require much accessories as the fuchsia pink shirt is already a bold piece.

You may opt to wear a pair of gold or silver studded earrings, a black mini shoulder bag and a pair of pink heels.

How To Style An Oversized Shirt - 20 Outfit Ideas & Styling Tips | Travel Beauty Blog
Photo: Depositphotos

3. Oversized Asymmetrical Cardigan with Skirt

The oversized top trend is not only limited to the hot summer months.

You can wear this trend during spring or fall too.

An oversized asymmetrical cardigan with a black knee-high skirt and low strapped heels does the trick.

How To Style An Oversized Shirt - 20 Outfit Ideas & Styling Tips | Travel Beauty Blog
Photo: Depositphotos

How To Style An Oversized Shirt (White):

4. Oversized Shirt and Biker Shorts

Baggy and loose fitting doesn’t necessarily mean boring.

Take things up a notch with an unbuttoned white oversized shirt and black biker shorts.

Show some skin, by dropping one of the sleeves below your bra, off the shoulder.

To accentuate your curves, fasten the shirt at the tummy with a wide black leather belt.

Wear gold statement earrings, some gold bangles and a pair of heels to complement the outfit.

How To Style An Oversized Shirt - 10 Styling Tips | Travel Beauty Blog
Photo: Depositphotos
How To Style An Oversized Shirt - 32 Outfit Ideas To Copy

5. Oversized Denim Jacket with Denim Bottoms

Nothing beats a classic denim on denim look – one of my favourite ways to style an oversized shirt.

There are multiple ways to sport the denim on denim trend.

Some options being: a blue oversized puff sleeve sweater with blue high waist denim shorts with blue denim ankle boots.

Or an oversized blue denim shirt with flower detail and straight boot cut jeans with blue denim ankle booties.

Lastly, oversized floral detailed blue patterned denim jacket with a mini blue denim skirt and black heels.

How To Style An Oversized Shirt - 10 Styling Tips | Travel Beauty Blog
Photo: Depositphotos
How To Style An Oversized Shirt - 32 Outfit Ideas To Copy

6. White Oversized Button Down Shirt with Red Trousers

How To Style An Oversized Shirt (White):

Working in corporate or have a business meeting to attend?

This is a great way to dress up your oversized white shirt but still keeping it classy.

3/4 sleeves white oversized shirt appropriately buttoned down to the shoulders, chucked inside a pair of bright red trousers.

A silver necklace and a Michael Kors bag to top off the look.

How To Style An Oversized Shirt - 10 Styling Tips | Travel Beauty Blog
Photo: Depositphotos

7. Cropped Oversized Jacket with Jeans Pants

Blush pink cropped oversized jacket layered over a beige camisole with a high-waisted light blue washed out denim pants.

Add a pop of color by going with a pair of bright pink pumps.

How To Style An Oversized Shirt - 10 Styling Tips | Travel Beauty Blog
Photo: Depositphotos

8. Oversized Shirt as a Dress

How To Style An Oversized Shirt (Silk Black):

If the oversized shirt is long enough you can wear it on its own as a dress.

Slightly unbuttoned and worn off the shoulder on one side.

Coupled with a black buckled belt to draw attention to your shape and a black crossbody bag to accessorize.

This look is perfect for date night, an evening out with the girls or for heading to the club.

Optionally, you may want to wear a black short pants or leggings to be less revealing.

How To Style An Oversized Shirt - 10 Styling Tips | Travel Beauty Blog
Photo: Depositphotos

9. Oversized Lined Shirt Short Pants Suit

The perfect outfit for summer: a green oversized linen shirt and matching linen shorts with a white cropped camisole inside.

Enhance the suit with a black hat and dark brown shoulder bag.

How To Style An Oversized Shirt - 10 Styling Tips | Travel Beauty Blog
Photo: Depositphotos
How To Style An Oversized Shirt - 32 Outfit Ideas To Copy

10. Oversized Shirt with Blue Distressed Mom Jeans

How To Style An Oversized Shirt (White Cotton):

A white oversized shirt worn half up, half down with a light blue-washed distressed mom jeans.

To imitate this style, simply stick one front end of the shirt into the pants while the other side hangs out.

Roll up the sleeves midway up your arm, put on a pair of white sneakers and you’re good to go.

How To Style An Oversized Shirt - 20 Outfit Ideas & Styling Tips | Travel Beauty Blog
How To Style An Oversized Shirt - 32 Outfit Ideas To Copy

11. Cropped Trench with Biker Playsuit

Elevate your outfit from basic to stylish, with a oversized cropped trench coat.

Remix the fit: Instead of just wearing a boring black biker playsuit, dress it up with a cropped trench coat, a pair of white sneakers and oversized sunglasses.

How To Style An Oversized Shirt - 20 Outfit Ideas & Styling Tips | Travel Beauty Blog
Photo: Depositphotos

12. Oversized Cropped Shirt with Black Pants

How To Style An Oversized Shirt (Cropped/Striped):

This oversized shirt encompasses a lot of different qualities at the same time.

Its striped, cropped, tiered and oversized with statement sleeves.

Since this oversized cropped shirt is very eye-catching.

To keep the attention on it, dress it down with a pair of loose fitting black pants.

How To Style An Oversized Shirt - 10 Styling Tips | Travel Beauty Blog
Photo: Depositphotos

13. Oversized Blazer with Trousers

If you’re wearing a blush pink one-button oversized blazer, style it with a complementary color tailored trousers.

Ideal for wearing to the office or to attend a business meeting.

Additionally, complete the look with a small matching handbag and heeled sandals.

How To Style An Oversized Shirt - 20 Outfit Ideas & Styling Tips | Travel Beauty Blog
Photo: Depositphotos
How To Style An Oversized Shirt - 32 Outfit Ideas To Copy

14. Oversized White Shirt with Double-breasted Vest

How To Style An Oversized Shirt:

Armless, black and white, double-breasted, tweed jacket styled to perfection over a white oversized shirt.

Jazz it up with black ankle boots and a clear Chanel bag.

How To Style An Oversized Shirt - 20 Outfit Ideas & Styling Tips | Travel Beauty Blog
Photo: Depositphotos

15. Oversized Armless Button-up Blouse with Khaki Trousers

Show off your shoulders in this light pink oversized, padded-shoulder, armless button-up blouse.

Tucked inside a brown baggy khaki trousers or joggers, with a black statement belt and a light red bag.

How To Style An Oversized Shirt - 10 Styling Tips | Travel Beauty Blog
Photo: Depositphotos

16. Oversized White Striped Shirt over a Turtleneck Top

How To Style An Oversized Shirt (Striped):

For the fall and winter months, throw a white striped oversized shirt over a black turtle neck top.

Complete the ensemble with silver statement earrings, wide leg pants, black pumps, a mini handbag and sunglasses.

How To Style An Oversized Shirt - 10 Styling Tips | Travel Beauty Blog
Photo: Depositphotos

17. Super Oversized Coat with Oversized Pants

It doesn’t get more comfortable than this super oversized purple coat matched with a neutral color cami top and blue baggy satin pants.

Related: How To Wear A Wide Leg Pants Outfit

Accessorized with oversized sunglasses and a Christian Dior bag.

This styling choice is definitely very laid back and cozy.

See Also
These Stylish Long Denim Skirt Outfits are bringing back the 90s Nostalgia | Travel Beauty Blog

Ideal for those days when you don’t feel like dressing up – its like you’re not wearing any clothes.

How To Style An Oversized Shirt - 10 Styling Tips | Travel Beauty Blog
Photo: Depositphotos

18. Oversized Bell Sleeves Shirt with Wide Leg Jeans

How To Style An Oversized Shirt (Bell Sleeves):

Tomboy style: A patterned Salvatore Ferragamo oversized shirt with black wide leg jeans.

A matching Salvatore Ferragamo men’s baseball cap turned backwards, a complementary Salvatore Ferragamo monogram bag and black patent platform shoes.

How To Style An Oversized Shirt - 20 Outfit Ideas & Styling Tips | Travel Beauty Blog
Photo: Depositphotos

19. Blue Oversized Shirt with White Wide Leg Pants

How To Style An Oversized Shirt:

You can turn your oversized shirt into a cropped top by only utilizing 2-3 buttons, tied to the front while both sleeves are worn off the shoulders, like pictured below.

Complete the look with white wide leg pants and a pair of black pointy toe pumps.

How To Style An Oversized Shirt - 10 Styling Tips | Travel Beauty Blog
Photo: Depositphotos

20. All Pink Oversized Pants Suit

How To Style An Oversized Satin Shirt (Pink):

When you’re going with bold colors like bright pink, use either white to highlight or black to tone down.

Related: How To Master The Barbiecore Outfit Trend

In this case, a cropped white mini top inside of a loose-fit fuchsia pink satin pants suit are bound to turn heads.

Take it further with black suede pumps, sunglasses and a white handbag.

How To Style An Oversized Shirt - 20 Outfit Ideas & Styling Tips | Travel Beauty Blog
Photo: Depositphotos

21. Cropped Oversized Shirt with Black Pencil Skirt

How To Style An Oversized Shirt (White/Cropped):

I think this cropped white oversized blouse and black pencil skirt makes a great office attire. You only need a pair of black pumps to finish this outfit.

How To Style An Oversized Shirt - 10 Styling Tips | Travel Beauty Blog
Photo: Depositphotos

22. Oversized Jacket Pants Suit

How To Style An Oversized Shirt (Brown):

There are so many ways to get on board with the oversized shirt trend and that includes business attire as well.

How beautiful is this brown oversized jacket suit with matching brown pumps and a contrasting color bag.

How To Style An Oversized Shirt - 20 Outfit Ideas & Styling Tips | Travel Beauty Blog
Photo: Depositphotos

23. Oversized Orange Sweater

Keep it simple. Pair a sweater with baggy satin pants and an oversized handbag.

How To Style An Oversized Shirt - 20 Outfit Ideas & Styling Tips | Travel Beauty Blog
Photo: Depositphotos

24. Oversized Blazer with Midi Skirt

How To Style An Oversized Shirt (Moss Green)

Show off a little skin for summer by wearing a moss green blazer over a dark green bra and a beige midi skirt.

Complement the ensemble with a pair of white Bottega Veneta sandals, white Dior bag and gold fashion jewelry.

How To Style An Oversized Shirt - 20 Outfit Ideas & Styling Tips | Travel Beauty Blog
Photo: Depositphotos

25. Pink Satin Shirt with V-Neck Dress

How To Style An Oversized Shirt (Satin Pink)

What another fun way to style a fuchsia pink oversized satin blouse; this time with a twist.

This one has a cowl neck with popcorn sleeves, styled below a black loose fitting v-neck satin dress.

Completed with sunglasses, a crossbody Dior saddle bag and matching fuchsia pink ankle heeled bootie.

How To Style An Oversized Shirt - 10 Styling Tips | Travel Beauty Blog
Photo: Depositphotos

26. Oversized Checked Blazer with Biker Shorts

Black and white checked blazer with black biker shorts and a black slim belt slightly fastened at the waist.

Another smart-casual look but not exactly appropriate for any formal business settings.

But you can easily switch out the biker shorts for a pair of trousers or a skirt if needed..

27. Oversized White Linen Shirt with Linen Shorts

How To Style An Oversized Shirt (White Linen)

An oversized white linen shirt with a white cami top and pair of brown linen shorts.

Dressed up with gold hoop earrings, layered gold necklace and a brown handbag.

How To Style An Oversized Shirt - 10 Styling Tips | Travel Beauty Blog
Photo: Depositphotos

28. Oversized Cropped Cardigan with Long Pants

Baby blue off-the-shoulder popcorn sleeves cropped sweater with light blue roomy long pants. Suited with a mint green handbag and matching heeled sandals.

How To Style An Oversized Shirt - 10 Styling Tips | Travel Beauty Blog
Photo: Depositphotos

29. Oversized Baby Pink Shirt and Skirt

Create a sophisticated look by pairing up a baby pink oversized shirt popped inside a matching baby pink diaper waist, flowy mini skirt.

How To Style An Oversized Shirt - 20 Outfit Ideas & Styling Tips | Travel Beauty Blog
Photo: Depositphotos

30. Oversized White Skirt with Animal Print Midi Skirt

How To Style An Oversized Shirt

White oversized shirt thrusted inside a brown snakeskin midi skirt.

A vintage mini Fendi bag and black sandals to enhance the ensemble.

How To Style An Oversized Shirt - 10 Styling Tips | Travel Beauty Blog
Photo: Depositphotos

31. Classic Oversized Trench Coat

I love this oversized tan trench coat over a white vest, with blue mom jeans, a white bag and classic vintage Chanel color-block cap toe CC slingback shoes.

How To Style An Oversized Shirt - 20 Outfit Ideas & Styling Tips | Travel Beauty Blog
Photo: Depositphotos

32. Oversized Shirt with Black Jeans Shorts

How To Style An Oversized Shirt

White oversized shirt unbuttoned, tucked into a pair of black jeans shorts.

Styled with a simple shoulder bag and black ankle boots.

How To Style An Oversized Shirt - 10 Styling Tips | Travel Beauty Blog
Photo: Depositphotos

Wrapping Up How To Style An Oversized Shirt

Key pointers to remember when going for an oversized shirt look:

  • Don’t limit yourself to a basic white shirt. Incorporate oversized sweaters, coats, tees and blazers. Include bold colors, detailed pieces and patterns.
  • Dress for the occasion. Keep it classy.
  • Size up your shirt appropriately – go 2-3 sizes up from your regular size so that it fits loosely around your waist and shoulders. This would also allow the shirt to be a few inches longer than a typical shirt.

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Last Updated on February 25, 2024 by Shevy

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